Methanol → Methyl 2-amino-3-(thiophen-2-yl)propanoate hydrochloride

HRID 255622Notes

Reaction equation

HRID 255622 reaction equation
S(Cl)([Cl:3])=O.[CH3:5]O.Cl.[S:8]1[CH:12]=[CH:11][CH:10]=[C:9]1[CH2:13][CH:14]([C:16]([OH:18])=[O:17])[NH2:15]>>[ClH:3].[CH3:5][O:17][C:16](=[O:18])[CH:14]([CH2:13][C:9]1[S:8][CH:12]=[CH:11][CH:10]=1)[NH2:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 201658013-(2-thienyl)-DL-alanine hydrochloride

Product 1

HCID 67438693Methyl 2-amino-3-(thiophen-2-yl)propanoate hydrochlorideYield 100.1%

Procedure

3.78 g (0.0318 mole) of thionyl chloride were added dropwise at -5° C. to 10.2 g (0.318 mole) of methanol. After 5 minutes, 3.3 g (0.0159 mole) of 3-(2-thienyl)-DL-alanine hydrochloride were added gradually to this solution, whilst keeping the temperature at -5° C. The mixture was then stirred for 3 hours at this temperature, and then left standing for 24 hours at room temperature. The reaction product was then condensed by evaporation under reduced pressure, and ethanol was added to the residue. The mixture was then condensed by evaporation under reduced pressure and 3.53 g (yield 100%) of 3-(2-thienyl)-DL-alanine methyl ester hydrochloride melting at 110°-112° C. were obtained as the residue.

Workup

  1. customat -5° C
  2. waitleft
  3. waitstanding for 24 hours at room temperature
  4. customcondensed
  5. customby evaporation under reduced pressure, and ethanol
  6. additionwas added to the residue
  7. customcondensed
  8. customby evaporation under reduced pressure

Sources & evidence

ORD record
ord-b1f06b06f8e6482da9b20ed123e3053b
Source dataset
uspto-grants-1987_10
Patent number
US04698329

Reaction notes

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